Dyestuff



Patented Apr. 21, 1925.

UNITED STATES' PATENT OFFICE.

GUILLAUME DE uoN'rmoLmN AND GERALD BoNnorE, or BASEL, SWITZERLAND, AS- SIGNORS TO SOCIETY or CHEMICAL INDUSTRY IN BASLE, or BASEL, swrrznn- LAND.

DYrsrurr.

No Drawing.

To all whom it may concern:

Be it known that we GUILLAUMEHDE MONTMOLLIN and GERALD BoNno'rn, both citizens of, the Swiss Confederation, and

residing at Basel, Switzerland, have in vented new and useful Dyestuffs, of which the following is a full, clear, and exact specification.

This invention relates to new dyestuffs, 1o valuable for the production of fast tints on acetyl cellulose. Itcomprises the new dyestuffs as well as the material dyed with same, 1

It has been found that new dyestufi's are obtained by combining non-hydroxylated nitro-diazo com ounds with aromatic monoamines of the from metanilic acid and substituted at their nitrogen atom by a residue containing a benzene nucleus, the two components being selected in such a way that only one contains a sulfonic group.

These dyestufl's correspond to the general formula v R. m-n-N-nr-N wherein R represents a non-hydroxylated 1 benzene nucleus carrying at least one nitro-,

0 group, R, a benzene nucleus not having any sulfonic group attached in ortho-position to a the azo-bridge and carrying the -blue and greenish-black powders, dissolving in water to yellow to brown and bluish- ML red solutions. They yield on, acetyl cellulose, when dyed in a feebly acid or neutral bath, from yellow to bluish-red and brown tints of good fastness to washing and of good to very good fastness to light.

enzenes series not derived- A pplicationvfiled July 29, 1924. Serial No. 728,953.

7 The following examples illustrate the inventlon.

Example 1.

0, 1, N. 0,11, on, 06H, some i The formation of the dyestufi' occurs very rapidly and as soon as the diazo-compound has dlsappeared, the dyestufi' is filtered and dried. It forms a bronzy powder, dissolving in water to a bluish-red solution and dyeing acetyl cellulose in an acetic acid bath fast bluish-red tints.-

The structural formula for the dyestufi is as follows:

aw. a

207 parts of 2 :6-dichlorol-nitraniline are converted into a the corresponding diazocompound by introducing them into a solution' of the calculated quantity of nitrosylsulfate in concentrated sulfuric acid and pouring the mixture on ice. The liquid of reaction is introduced, while stirring, into a solution of 271 parts of diphenylaminsulfonate of sodium, whereby the formation of the dyestufl occurs immediately.- .Stirring is continued for some time, whereupon the mass is filtered and dried. The dyestuif forms a dark brown powder, dissolving in water to an orange solution and dyeing acetyl cellulose in an acetic acid bath orange tints of remarkable fastness to light.

Emample 3.

bath orange-red tints of remarkable fastness to light.

The following table shows the principal properties of some of the dyestuffs prepared according to the present invention.

Tint on Diazotizing Coupling Aspect of the gawk component. component. dyestufi powder. ceuulosm m-Nitraniline.-. E thy! b e nzyl Orange Yellow.

aniline sultonie acid. 2-chloro-4-nido Vio1et-brown Pink.

traniline. 21 D initr anl- .....do Blackish-violet Bluish-red.

me. 2:6-Dichloro-4- Diphenylam- Brownish-black. Orange.

nitraniline. in talsulionic aci 4-Ch1oro-2-ni- Ethylbenzyl- Reddish-brown. Do.

traniline. aniline-sulionic acid. 4-Nitraniline-2 Methyidxph e- Violet-brown. R e d d i s h sulfonic acid. nylaunne. brown. 2-Nitraniline-4- Diphenylamine. Greenish-black.. Orange-red.

sulionlc acid. 4-Nitraniline-3- .-...do Yellowish-- Do.

suifonic acid. brown. 2:4-Dinitraniline. Ben z yiamline- Gray-black R e 1 dis h suliomc acid. brown. m-Nitraniline.... 0 Yellow-orange... Yellow.

What we claim is: 1. As new products the new dyestufis of the general formula:

Wherein R represents a non-hydroxylated benzene nucleus carryin at least one nitrogroup, R a benzene nuc eus not having any sulfonic group attached in ortho-position to the azo-bridge and carrying the dissolving in water to orange to brown and bluish-red solutions, and yielding on acetyl cellulose, when dyed in a feebly acid or neutral bath, from yellow to bluish-red and brown tints of good fastness to washing and of good to very good fastness to light.

2. As new products the new dyestuffs of the general formula:

wherein R, represents a non-hydroxylated benzene nucleus carrying at least one nitrogroup, R a benzene nucleus not having any sulfonic group attached in ortho-position to the azo-bridge and carrying the J I\\R0 group in para-position to the azo-bridge, R a benzyl residue, and R, hydrogen or alkyl, and in which only one of the residues R R R contains one sulfonic group, which dyestuffs form from yellowish-brown to blackish-violet and greenish-black powders. dissolving in water to orange to brown and bluish-red solutions, and yielding on acetyl cellulose, when dyed in a feebly acid or neutral bath from orange to bluish-red tints of good fastness to washing and of good to very good fastness to light.

3. As a new product the new dyestufi of the formula:

iO ciir-oeni-soin .e. l t

which forms a bronzy powder, dissolving in water to a bluish-red solution and yielding on acetyl cellulose, when dyed in: an acetic acid bath, bluish-red tints of good fastness to washing and very good fastness to light.

4. The material dyed with the dyestuffs of claim 1.

5. The material dyed with the dyestuffs of claim 2.

c. The material dyed with the dyestufi' of 

